Mary Wotton, Lady Guildford (1499–after 1527), calmly gazes at the viewer from within a grand setting embellished by a marble column decorated in an Italianate style. She and her husband, Sir Henry Guildford, were among Holbein’s most important patrons during the artist’s first stay in England. While the sophisticated backdrop, jewelry, and fashionable dress, painted using lavish quantities of gold, denote Lady Guildford’s social status, the portrait also aims to communicate her piety and virtue. She clutches a religious book and a rosary, as if caught in a moment of reading or praying. The sprig of rosemary attached to her bodice is a traditional symbol of remembrance.

Written in an animated and accessible style, this popular work, long attributed to St. Bonaventure, encourages readers to reflect on mortality—hence the “mirror” in the English title—and contemplate the episodes of suffering that led up to Christ’s death. The woodcut illustration shows St. Bonaventure giving the book to a woman, suggesting that the text was specifically intended for a female readership or that this edition was particularly marketed to women. In Holbein’s portrait of Lady Guildford, the sitter holds what might be a copy of this text: an elegant green volume with a tasseled bookmark, labeled by Holbein with its Latin title, Vita Christi (Life of Christ), along the book’s top edge.

Although this panel is one of Holbein’s masterpieces, the dignified sitter, dressed in an ermine fur cap and a fine silk shawl, remained unidentified until 2004, when the animals in the portrait were recognized as likely references to the Lovell family. Anne Lovell (née Ashby; d. 1539) was a wealthy English noblewoman whose husband, Sir Francis Lovell, served King Henry VIII. Her pet red squirrel, restrained by a silver chain and nibbling a hazelnut, alludes to the squirrels on the Lovell family crest. The starling on the left is a play on East Harling (commonly spelled as “Estharlyng” in Tudor times), the location of the Lovell estate in Norfolk, England. Technical studies have shown that Holbein added the animals at a late stage in the painting process, very likely at the request of the patrons.

Sir Nicholas Carew (ca. 1496–1539) carried out several important diplomatic missions in the service of Henry VIII. Made with a painted portrait in mind, this study exemplifies Holbein’s approach to drawing during his first stay in England. Working on a large scale and concentrating his attention on Carew’s face and beard, the artist modeled the man’s features by carefully blending black and colored chalks. Other parts of the drawing, such as the sitter’s upper body and the fluffy feathers that adorn his hat, are described using swiftly drawn yet virtuosic lines. The headgear is covered entirely in black chalk, but the letters gl, inscribed on the headband, would have reminded Holbein that the garment’s actual color was either yellow (gelb) or gold (gold).

With his right hand raised and his left resting on a book and clutching a pair of glasses, the scholar in Quentin Metsys’s painting appears to have been caught at a moment of revelation. His dynamic pose and bold physicality distinguish the man from Holbein’s more stoic, seemingly withdrawn sitters, such as Erasmus and Sir Thomas More. The scholar is situated against a window, with a carefully constructed vista extending into the distance, including a river, a forest, mountains, and a fortified city. Such views, known as world landscapes, were a specialty of Antwerp painters in the 1520s.

Jan Gossaert depicted this self-possessed sitter with a red cross emblazoned on his doublet, a gem-encrusted jewel shaped like a scallop shell hanging around his neck, and an intricate hat badge. Despite such seemingly specific attributes, the man’s identity was lost until the late twentieth century, when he was recognized as Francisco de los Cobos y Molina (ca. 1475/80– 1547), the powerful secretary and advisor to Emperor Charles V. The identification was made by comparing the painting with the portrait medal of Los Cobos.

Portrait medals, which unite a likeness, text (usually name and motto), and personal emblem, can play an important role in identifying distinguished individuals. This medal and its inscription reveal the subject of Jan Gossaert’s corresponding painting. Although it can be challenging to directly compare works of such different mediums, the men’s facial features, hairstyles, and beards appear strikingly similar. Moreover, in both images the sitter wears the scallop-shell pendant of the Order of Santiago, of which Los Cobos was comendador mayor (major commander).